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Ultrasound-assisted facile and efficient synthesis of novel Benzoxazole derivatives from o-aminocardanol using Indion 190 resin as a reusable catalyst

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Abstract

A mild, convenient, and green route for synthesizing benzoxazole derivatives has been developed using o-aminocardanol and readily available aromatic aldehydes in the presence of Indion 190 resin as a heterogeneous catalyst under ultrasonic irradiation. The reaction was carried out under a greener and eco-friendly solvent to afford the desired products in good yields. The reaction has good tolerance towards a wide variety of electron-donating, electron-withdrawing, polyaromatic and heterocyclic aldehydes. Moreover, the heterogeneous catalyst Indion 190 resin was recovered and reused several times without significantly losing its catalytic activity.

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SYNOPSIS An efficient, eco-friendly, and recyclable Indion 190 catalyst was used to prepare novel benzoxazole derivatives of various aldehydes and o-aminocardanol under ultrasonic irradiation (US). A short reaction time, higher yields, easy workup, and tolerability toward the variety of functional groups are the present method's key advantages, which give economic and ecological rewards.

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References

  1. McKee M L and Kerwin S M 2008 Synthesis, Metal ion binding, and biological evaluation of new anticancer 2-(2′-hydroxyphenyl)benzoxazole analogs of uk-1 Bioorg. Med. Chem. 16 1775

    Article  CAS  Google Scholar 

  2. Mortimer C G, Wells G, Crochard J P, Stone E L, Bradshaw T D, Stevens M F and Westwell A D 2006 Antitumor benzothiazoles. 2,6(1) 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (GW 610, NSC 721648), a simple fluorinated 2-arylbenzothiazole, shows potent and selective inhibitory activity against lung, colon, and breast cancer cell lines J. Med. Chem. 49 179

    Article  CAS  Google Scholar 

  3. Pal S, Manjunath B, Ghorai S and Sasmal S 2018 Benzoxazole alkaloids: occurrence, chemistry, and biology The Alkaloids: Chem. Biol. 79 71

    CAS  Google Scholar 

  4. Agag T, Liu J, Graf R, Spiess H W and Ishida H 2012 Benzoxazole resin: a novel class of thermoset polymer via smart benzoxazine resin Macromolecules 45 8991

    Article  CAS  Google Scholar 

  5. Kok S H L, Gambari R, Chui C H, Yuen M C W, Lin E, Wong R S M, et al. 2008 Synthesis and anti-cancer activity of benzothiazole containing phthalimide on human carcinoma cell lines Bioorg. Med. Chem. 16 3626

    Article  CAS  Google Scholar 

  6. Katsura Y, Inoue Y, Tomoi M and Takasugi H 1992 Studies on Antiulcer Drugs. V. Synthesis and antiulcer activity of aralkylbenzazoles Chem. Pharm. Bull. 40 2062

    Article  CAS  Google Scholar 

  7. Yamato M 1922 Study on the development of biological-active compounds after the model of natural products Yakugaku Zasshi 112 81

    Article  Google Scholar 

  8. Boyer J, Arnoult E, Medebielle M, Guillemont J, Unge J and Jochmans D 2011 Difluoromethylbenzoxazole pyrimidine thioether derivatives: a novel class of potent non-nucleoside hiv-1 reverse transcriptase inhibitors J. Med. Chem. 54 7974

    Article  CAS  Google Scholar 

  9. Guennic B L, Chibani S, Charaf-Eddin A, Massue J, Ziessel R, Ulrich G and Jacquemin D 2013 The NBO pattern in luminescent chromophores: unravelling excited-state features using TD-DFT Phys. Chem. Chem. Phys. 15 7534

    Article  Google Scholar 

  10. Xue P, Chen P, Jia J, Xu Q, Sun J, Yao B, et al. 2014 A triphenylamine-based benzoxazole derivative as a high-contrast piezofluorochromic material induced by protonation Chem. Commun. 50 2569

    Article  CAS  Google Scholar 

  11. Stephens F F and Bower J D 1949 The preparation of benziminazoles and benzoxazoles from Schiff’s bases. Part I J. Chem. Soc. 0 2971

    Article  CAS  Google Scholar 

  12. Evindar G and Batey R A 2006 Parallel synthesis of a library of benzoxazoles and benzothiazoles using ligand-accelerated copper-catalyzed cyclizations of ortho-halobenzanilides J. Org. Chem. 71 1802

    Article  CAS  Google Scholar 

  13. Pivsa A S, Satoh T, Kawamura Y, Miura M and Nomura M 1998 Palladium-catalyzed arylation of azole compounds with aryl halides in the presence of alkali metal carbonates and the use of copper iodide in the reaction Chem. Soc. Jpn. 71 467

    Article  Google Scholar 

  14. Villemin D, Hammadi M and Martin B 1996 Clay Catalysis: Condensation of orthoesters with o-substituted aminoaromatics into heterocycles Synth. Commun. 26 2895

    Article  CAS  Google Scholar 

  15. Doise M, Dennin F, Blondeau D and Sliwa H 1990 Synthesis of novel heterocycles: Oxazolo[4,5-b]pyridines and oxazolo[4,5-d]pyrimidines Tetrahedron Lett. 1 1155

    Article  Google Scholar 

  16. Jenkins G, Knevel A and Davis C 1961 Notes. a new synthesis of the benzothiazole and benzoxazole rings J. Org. Chem. 26 274

    Article  CAS  Google Scholar 

  17. Hein D W, Alheim R J and Leavitt J J 1957 The use of polyphosphoric acid in the synthesis of 2-aryl- and 2-alkyl-substituted benzimidazoles, benzoxazoles and benzothiazoles J. Am. Chem. Soc. 79 427

    Article  CAS  Google Scholar 

  18. Salehi P, Dabiri M, Zolfigol M A, Otokesh S and Baghbanzadeh M 2006 Selective synthesis of 2-aryl-1-arylmethyl-1H-1,3-benzimidazoles in water at ambient temperature Tetrahedron Lett. 47 2557

    Article  CAS  Google Scholar 

  19. Bachhav H M, Bhagat S B and Telvekar V N 2011 Efficient protocol for the synthesis of quinoxaline, benzoxazole and benzimidazole derivatives using glycerol as green solvent Tetrahedron Lett. 52 5697

    Article  CAS  Google Scholar 

  20. So Y H and Heeschen J P 1997 Mechanism of polyphosphoric acid and phosphorus pentoxide−methanesulfonic acid as synthetic reagents for benzoxazole formation J. Org. Chem. 62 3552

    Article  CAS  Google Scholar 

  21. Pottorf R S, Chadha N K, Katkevics M, Ozola V, Suna E, Ghane H, et al. 2003 Parallel synthesis of benzoxazoles via microwave-assisted dielectric heating Tetrahedron Lett. 44 175

    Article  CAS  Google Scholar 

  22. Chakraborti A K, Rudrawar S, Kaur G and Sharma L 2004 An efficient conversion of phenolic esters to benzothiazoles under mild and virtually neutral conditions Synlett 35 1533

    Article  Google Scholar 

  23. Kamble O, Chatterjee R, Dandela R and Shinde S 2022 Ultrasonic energy for construction of bioactive heterocycles Tetrahedron 120 132893

    Article  CAS  Google Scholar 

  24. Rambabua D, Kumar S K, Sreenivas B Y, Sandra S, Kandale A, Misra P, et al. 2013 Ultrasound-based approach to spiro-2,3-dihydroquinazolin-4(1H)-ones: their in vitro evaluation against chorismate mutase Tetrahedron Lett. 54 495

    Article  Google Scholar 

  25. Kondo E and Kanai K 1972 The lethal effect of long-chain fatty acids on mycobacteria Jpn. J. Med. Sci. Biol. 25 1

    Article  CAS  Google Scholar 

  26. Dubos R J 1950 effect of organic acids on mammalian tubercle bacilli J. Exp. Med. 92 319

    Article  CAS  Google Scholar 

  27. Mali J K, Sutar Y B, Pahelkar A R, Verma P M and Telvekar V N 2020 Novel fatty acid-thiadiazole derivatives as potential antimycobacterial agents Chem. Biol. Drug Des. 95 174

    Article  CAS  Google Scholar 

  28. Tyman J H P 1979 Non-isoprenoid long chain phenols Chem. Soc. Rev. 8 499

    Article  CAS  Google Scholar 

  29. Maqbool H G, Chandra S D, Kumarswamy B E and Pai V K 2013 Cyclic voltammetric studies of synthesized cardanol based azo dyes Res. J. Chem. Sci. 3 44

    CAS  Google Scholar 

  30. Lubi M C and Thachil E T 2000 Cashew nut shell liquid (CNSL) - a versatile monomer for polymer synthesis Des. Monomers. Polym. 3 123

    Article  CAS  Google Scholar 

  31. Ni C L, Song X H, Yan H, Song X Q and Zhong R G 2010 Improved synthesis of diethyl 2, 6-dimethyl-4-aryl-4H-pyran-3,5-dicarboxylate under ultrasound irradiation Ultrason. Sonochem. 17 367

    Article  CAS  Google Scholar 

  32. Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi H R and Mirzaei P 2010 Ultrasound-assisted one-pot, three-component synthesis of spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,6′(1′H)-diones in water Ultrason. Sonochem. 17 447

    Article  CAS  Google Scholar 

  33. Zhang Z H, Li J J and Li T S 2008 Ultrasound-assisted synthesis of pyrroles catalyzed by zirconium chloride under solvent-free conditions Ultrason. Sonochem. 15 673

    Article  CAS  Google Scholar 

  34. Khosropour A R 2008 Ultrasound-promoted greener synthesis of 2,4,5-trisubstituted imidazoles catalyzed by Zr(acac)4 under ambient conditions Ultrason. Sonochem. 15 659

    Article  CAS  Google Scholar 

  35. Hallett J P and Welton T 2011 Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis Chem. Rev. 111 3508

    Article  CAS  Google Scholar 

  36. Navarro N M, Chave T, Pochon P, Bisel I and Nikitenko S I 2011 Effect of ultrasonic frequency on the mechanism of formic acid sonolysis J. Phys. Chem. B 115 2024

    Article  CAS  Google Scholar 

  37. Riesz P, Berdahl D and Christman C L 1985 Free radical generation by ultrasound in aqueous and nonaqueous solutions Environ. Health Perspect. 64 233

    Article  CAS  Google Scholar 

  38. Srivastava R M, Neves F R A, da Silva C A and Bortoluzzi A J 2009 First ultrasound-mediated one-pot synthesis of N-substituted amides Ultrason. Sonochem. 16 737

    Article  CAS  Google Scholar 

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All authors contributed equally.

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Authors and Affiliations

  1. Department of Chemical Engineering, Institute of Chemical Technology, Mumbai, 400019, India

    Bhagwat R Patil, Dipak V Pinjari & Aniruddha B Pandit

  2. Institute of Chemical Technology, Mumbai, Marathwada Campus, Jalna, 431203, India

    Navnath T Hatvate & Atul H Bari

Authors
  1. Bhagwat R Patil
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  2. Navnath T Hatvate
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  3. Atul H Bari
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  4. Dipak V Pinjari
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  5. Aniruddha B Pandit
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Correspondence to Aniruddha B Pandit.

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Patil, B.R., Hatvate, N.T., Bari, A.H. et al. Ultrasound-assisted facile and efficient synthesis of novel Benzoxazole derivatives from o-aminocardanol using Indion 190 resin as a reusable catalyst. J Chem Sci 135, 4 (2023). https://doi.org/10.1007/s12039-022-02120-7

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  • DOI: https://doi.org/10.1007/s12039-022-02120-7

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